EP1342742B1 - Agent d'étanchéité a base de silicone a durcissement a temperature ambiante - Google Patents

Agent d'étanchéité a base de silicone a durcissement a temperature ambiante Download PDF

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Publication number
EP1342742B1
EP1342742B1 EP02004869A EP02004869A EP1342742B1 EP 1342742 B1 EP1342742 B1 EP 1342742B1 EP 02004869 A EP02004869 A EP 02004869A EP 02004869 A EP02004869 A EP 02004869A EP 1342742 B1 EP1342742 B1 EP 1342742B1
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EP
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Prior art keywords
groups
weight
silanes
polysiloxane composition
parts
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EP02004869A
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German (de)
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EP1342742A1 (fr
Inventor
Michael Dr. Stenert
Hermann Block
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Evonik Operations GmbH
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Hanse Chemie AG
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Priority to DE50207717T priority Critical patent/DE50207717D1/de
Priority to AT02004869T priority patent/ATE335038T1/de
Priority to EP02004869A priority patent/EP1342742B1/fr
Priority to ES02004869T priority patent/ES2269533T3/es
Publication of EP1342742A1 publication Critical patent/EP1342742A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond

Definitions

  • the invention relates to a room temperature curable polysiloxane composition.
  • Room temperature curing polysiloxane or silicone compounds are used as so-called silicone sealants for many purposes.
  • Commonly used are one-component masses (RTV-1), which harden on access of atmospheric moisture. They usually contain hydroxy-functional polydiorganosiloxanes and silane crosslinkers, usually so-called oximesilanes. Upon ingress of atmospheric moisture, hydroxypolysiloxane and the silane crosslinker condense to give an alkanone oxime, usually butanone oxime.
  • RTV-1 room temperature curing polysiloxane or silicone compounds
  • oxime sealants are preferred in practice, since the properties can be varied over a wide range without great development effort and adapted to application requirements. They have very good storage capabilities.
  • butanone oxime During curing by condensation, butanone oxime is released as a cleavage product. Even at or immediately after the preparation of the mass butanone oxime is already released to some extent, since the butanone oxime silane added as a crosslinker is partially reacted with water present in the formulation constituents while cleaving butanone oxime is split off. The sealing compound not yet cured in the cartridge therefore always contains a certain proportion of butanone oxime.
  • Butanone oxime is suspected to be carcinogenic. From 1 July 2002, all packaging containing more than 1% butanone oxime will have to be labeled. This proportion is in the usual RTV-1 based on oxime by the at Production occurring and above-described side reactions usually reached or exceeded.
  • alkoxy sealants On curing, hydroxy-functional polysiloxanes are reacted here with alkoxysilanes as crosslinkers.
  • alkoxy-based RTV-1 The formulation of such alkoxy-based RTV-1 is problematic in that storage stability is reduced and in any case a suitable catalyst must be present to facilitate curing.
  • the present invention has for its object to provide a polysiloxane composition of the type mentioned, which does not have the disadvantages of the oxime sealants mentioned and is easy to formulate.
  • room-temperature-curable polysiloxane composition or RTV is familiar to the person skilled in the art and is explained, for example, in Ullmanns Encyclopedia of Industrial Chemistry ", 5th edition, volume A 24, p. 72.
  • polysiloxanes must be crosslinkable. This means that they contain at least two functional groups which can react with the crosslinker also present. According to the invention it is provided that the polysiloxanes at least partially (not necessarily exclusively) acyloxy as functional crosslinkable groups. In the crosslinking process (condensation), the acyl group is split off as acid.
  • alkoxysilane crosslinker refers to silanes which contain alkoxy groups as functional groups capable of undergoing a crosslinking reaction (see, for example, Table 8 on the cited page of Ullmanns Encyclopedia).
  • the core of the invention is to provide acyloxy groups as functional groups instead of the hydroxy groups customary in the prior art in the crosslinkable polysiloxanes.
  • the alkoxysilanes already known per se in the prior art as a silane crosslinker and still achieve sufficient reactivity and thus rapid curing of the polysiloxane composition under the influence of atmospheric moisture, without any special requirements would be placed on the crosslinking catalyst.
  • the acyloxypolysiloxanes have a significantly higher reactivity with the alkoxysilanes than the hydroxy-functional polysiloxanes used in the prior art.
  • acetoxy sealants are already known in which hydroxypolysiloxanes react with acetoxysilane to cure. These acetoxy sealants are poorly used in the art because they cure to release corrosive acetic acid.
  • the invention utilizes the acetoxy groups as reactive functional groups on the polysiloxane rather than the silane and allows these acetoxy groups of the polysiloxane to condense during cure of the RTV mass with the less reactive alkoxy groups of the silane crosslinker.
  • the curing largely by condensation of acyloxy groups of the polysiloxane with alkoxy groups of the polysiloxane crosslinker takes place.
  • functional groups on the polysiloxanes other than acyloxy other functional groups such as. Hydroxy groups.
  • the silane crosslinkers may contain as functional groups further groups such as the butanone oxime groups known from the prior art.
  • the silane crosslinkers may combine alkoxy groups and other functional groups either in the same molecule or mixtures of silane crosslinkers having different functional groups may be included in the composition.
  • the proportion of oxime groups in the added silane crosslinking agent is preferably so low that the limit value of the butanone oxime fraction (1%) triggering a labeling obligation is not exceeded in the mass stored in the cartridge.
  • a particular advantage of the combination of the present invention with the oxime crosslinking of the prior art is that then in the curing reaction both small amounts of acid (usually acetic acid) and butanone oxime are released and that these two cleavage products are mutually in the form of an adduct tie. So bound butanone oxime is not a free butanone oxime, it is therefore not included in the mandatory labeling portion of butanone oxime. Due to the binding of the liberated acid, in addition a soiling of the cured mass or a corrosiveness thereof is avoided.
  • acyloxy groups provided according to the invention preferably have a hydrocarbon radical (in particular alkane radical) having 1 to 8 C atoms, which may be straight-chain or branched. Especially preferred as acyloxy groups are acetoxy groups.
  • the crosslinkable polysiloxanes are at least partially Polydiacyloxysiloxanes. Accordingly, the alkoxysilane crosslinkers at least partially preferably contain two or more alkoxy groups in one molecule.
  • alkoxysilane crosslinkers in the sense of the invention are silanes which are capable of crosslinking and contain at least one alkoxy group among the functional groups.
  • the invention further provides a process for the preparation of a polysiloxane composition according to the invention, in which reactive hydroxyl-containing polysiloxanes can be reacted with silanes containing acyloxy groups. Subsequently or simultaneously, the alkoxysilane crosslinker according to the invention is added.
  • the acyloxysilanes preferably contain at least two acyloxy groups.
  • the hydroxy-functional polysiloxanes give rise to the acyloxy-functional polysiloxanes provided according to the invention.
  • Crosslinkable polysiloxanes containing acyloxy groups as functional groups are formed in this first step.
  • the reactive hydroxy-containing polysiloxanes used in the first step of the reaction are preferably polydiorganosiloxanes, more preferably polydimethylsiloxanes.
  • ⁇ , ⁇ -functional polydiorganosiloxanes can be used.
  • the proportion of acyloxy-containing silanes based on the reactive hydroxy-containing polysiloxanes in the first process step is preferably 0.01-2 wt%, more preferably 0.05-1.5 wt%, more preferably 0.1-0 , 5 wt .-%.
  • k: 2 to 4 is preferred;
  • k + m + n . 4
  • the total amount of silane crosslinkers Alkoxysilanvernetzer and optionally other silane crosslinkers, for example, with oxime groups, based on the crosslinkable polysiloxanes, preferably at about 3-8% by weight.
  • both alkoxy and oxime silanes are used as silane crosslinkers
  • the molar ratio of alkoxy and oxime groups in this crosslinker is preferably between 1: 4 and 4: 1, more preferably between 1: 2 and 2: 1.
  • the methyl groups may be replaced by vinyl, phenyl, C 2 to C 8 -alkyl or haloalkyl groups.
  • the polysiloxanes are preferably substantially linear, but branched organosilyl units may also be present. Preferred viscosities of the polysiloxanes are between 0.1 and 1000 Pa.s, more preferably 1 and 100 Pa.s, more preferably 5 and 1000 Pa.s, particularly preferably 20 to 400 Pa.s.
  • plasticizers it is possible to use end-stopped polydiorganosiloxanes and / or liquid aliphatic or aromatic hydrocarbons, preferably in the molecular weight range from about 100 to 1000, whose volatility is low and their compatibility with polysiloxanes is adequate.
  • examples include paraffin oils, polysubstiusammlung alkylbenzenes or oligomeric, preferably branched C3 to C5 alkenes.
  • the viscosity of the plasticizers is preferably in the range 0.1-1 Pa ⁇ s.
  • Silane crosslinking agents usable in the invention are, for example, oxime silane .: tetraethoxysilane methyltrimethoxysilane methyltriethoxysilane vinyltriethoxysilane, ethyltrimethoxysilane, vinyltrimethoxysilane, Tetrabutanonoximsilan Methyltributanonoximsilan, Ethyltributanonoximsilan, Vinyltributanonoximsilan, Ethyltripropanonoximsilan, Vinyltripentanon (2), Dimethoxydibutanonoximsilan, Ethoxytributanonoximsilan, Trimethoxybutanonoximsilan, t-Butoxytributanonoximsilan, Dimethoxydibutanonoximsilan, Methylmethoxydibutanonoximsilan, Vinylmethoxydibutanonoxims
  • Preferred silanes used are: methyltrimethoxysilane, methyltriethoxysilane, tetrabutanone oxime silane, methyltributanonoxime silane, vinyltributanonoxime silane, vinyldimethoxybutanone oxime silane, methyldiethoxybutanone oxime silane and dimethoxy dibutanone oxime silane.
  • auxiliaries and fillers may be present.
  • auxiliaries are, for example, organic solvents, such as. Toluene, hexane, isoparaffins; also color pigments or organic acids, such as. For example, 2-ethylhexanoic acid, benzoic acid and dodecylbenzenesulfonic acid.
  • Fillers are preferably reinforcing and non-reinforcing fillers, such as.
  • pyrogenic or precipitated silica carbon black, quartz powder, precipitated or ground chalk, and metal oxides, sulfates, silicates, hydroxides, carbonates and / or bicarbonates.
  • the fillers may possibly be surface-modified. Mixtures of fillers of any composition can be used.
  • a preferred filler is fumed silica used as a thixotropic agent. It can be used untreated, hydrophilic or treated with different silanes, hydrophobic silica. Preference is given to using hydrophilic silica having a BET surface area of 100 to 300 m 2 / g.
  • adhesives such as aminosilanes, methacrylsilanes, epoxysilanes or mercaptosilanes.
  • organometallic compounds conventionally used for condensation-crosslinking polysiloxanes can be used, for example, dibutyltin dilaurate, dibutyltin diacetate, stannous octoate, and the like.
  • Catalysts based on titanium, zirconium or aluminum compounds are also usable.
  • Examples of the first reaction step of the inventive- ⁇ en method usable acyloxysilanes are tetraacetoxysilane, methyltriacetoxysilane, ethyltriacetoxysilane, dimethyldiacetoxysilane, Methylethoxydiacetoxysilan, Dimethoxydiacetoxysilan, Phenylmethoxydiacetoxysilan, Dibutoxydiacetoxysilan, trimethylacetoxysilane, Triethoxyacetoxysilan, Phenyldimethylacetoxysilan, Methyldibutoxyacetoxysilan, Dimethylmethoxyacetoxysilan, vinyltriacetoxysilane, propyltriacetoxysilane, Methylvinyldiacetoxysilan, Ethylvinyldiacetoxysilan, octyltriacetoxysilane, Octy
  • methyltriacetoxysilane ethyltriacetoxysilane, di-t-butoxydiacetoxysilane, trimethylacetoxysilane. If these silanes contain only one acyloxy group, they can only be used together with further acyloxysilanes having at least two acyloxy groups in the molecule.
  • the polysiloxane compositions according to the invention can be prepared in the prior art conventional mixing units, such as. As in planetary mixers, dissolvers, butterfly mixers or continuous mixing screws. The mixing of the components preferably takes place at room temperature.
  • MEKO content methyl ethyl ketone, decomposition product of butanone oxime
  • the calibration of the MEKO contents resulting from the examples and comparative examples was carried out by separate gas chromatographic measurements of different decalin / MEKO ratios and in particular by measurements on systems with a defined MEKO (wt .-%) and decalin content (wt .-%) ,
  • the MEKO content in the uncrosslinked product is 0.7% by weight.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III 0.3 parts by weight dimethyldiacetoxysilane IV 1.0 parts by weight Tetrakis (2-butanone oxime) silane, 2.5 parts by weight Vinyltris (2-butanone oxime) silane, 4.0 parts by weight vinyltrimethoxysilane be used.
  • the MEKO content in the uncrosslinked product is 0.6% by weight.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III 0.15 parts by weight ethyltriacetoxysilane, IV 4.5 parts by weight Methyltris (2-butanone oxime) silane, 3.0 parts by weight tetraethoxysilane be used.
  • the MEKO content in the uncrosslinked product is 0.7% by weight.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III 0.15 parts by weight ethyltriacetoxysilane, IV 3.0 parts by weight Vinyltris (2-butanone oxime) silane, 4.5 parts by weight methyltrimethoxysilane be used.
  • the MEKO content in the uncrosslinked product is 0.6% by weight.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III 0.15 parts by weight ethyltriacetoxysilane, IV 4.5 parts by weight Vinyltris (2-butanone oxime) silane, 3.0 parts by weight methyltrimethoxysilane be used.
  • the MEKO content in the uncrosslinked product is 0.8% by weight.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III 0.15 parts by weight methyltriacetoxysilane, IV 1.5 parts by weight Vinyltris (2-butanone oxime) silane, 6.0 parts by weight Dimethoxydi (2-butanone oxime) silane be used.
  • the MEKO content in the uncrosslinked product is 0.8% by weight.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III 0.15 parts by weight methyltriacetoxysilane, IV 1.5 parts by weight Vinyltris (2-butanone oxime) silane, 2.0 parts by weight Methytris (2-butanone oxime) silane, 3.5 parts by weight tetraethoxysilane be used.
  • the MEKO content in the uncrosslinked product is 0.5% by weight.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III 0.15 parts by weight methyltriacetoxysilane, IV 1.5 parts by weight Methyltris (2-butanone oxime) silane, 6.0 parts by weight Diethoxymono (2-butanone oxime) vinylsilane be used.
  • the MEKO content in the uncrosslinked product is 0.5% by weight.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III 0.3 parts by weight Di-tert-butoxydiacetoxysilane, IV 7.5 parts by weight Di (2-butanone oxime) ethoxyvinylsilane be used.
  • the MEKO content in the uncrosslinked product is 0.6% by weight.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III 0.3 parts by weight Di-tert-butoxydiacetoxysilane, IV 4.5 parts by weight Vinyltris (2-butanone oxime) silane 3.0 parts by weight tetramethoxysilane be used.
  • the MEKO content in the uncrosslinked product is 0.7% by weight.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III 0.3 parts by weight Di-tert-butoxydiacetoxysilane, IV 1.5 parts by weight Vinyltris (2-butanone oxime) silane, 2.5 parts by weight Methyltris (2-butanone oxime) silane, 2.5 parts by weight methyltrimethoxysilane be used.
  • the MEKO content in the uncrosslinked product is 0.5% by weight.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III 0.05 parts by weight trimethylacetoxysilane 0.10 parts by weight methyltriacetoxysilane IV 3.0 parts by weight Tetrakis (2-butanone oxime) silane 4.5 parts by weight methyltriethoxysilane be used.
  • the MEKO content in the uncrosslinked product is 0.7% by weight.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III 0.05 parts by weight trimethylacetoxysilane 0.10 parts by weight ethyltriacetoxysilane IV 6.0 parts by weight Tris (2-butanone oxime) methoxysilane 1.5 parts by weight vinyltrimethoxysilane be used.
  • the MEKO content in the uncrosslinked product is 0.6% by weight.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III 0.05 parts by weight trimethylacetoxysilane 0.10 parts by weight ethyltriacetoxysilane IV 5.0 parts by weight Tris (2-butanone oxime) methoxysilane 2.5 parts by weight vinyltrimethoxysilane be used.
  • the MEKO content in the uncrosslinked product is 0.4% by weight.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III a silane of the general formula R n (RO) m Si (O-Ac) k is not used IV 1.5 parts by weight Vinyltris (2-butanone oxime) silane 6.0 parts by weight Methyltris (2-butanone oxime) silane be used.
  • the MEKO content in the uncrosslinked product is 1.1% by weight.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III a silane of the general formula Rn (RO) m Si (O-Ac) k is not used IV 7.5 parts by weight Vinyltris (2-butanone oxime) silane be used.
  • the MEKO content in the uncrosslinked product is 1.2% by weight.
  • polysiloxane compositions prepared according to Comparative Examples 1 and 2 have sufficient shelf life and stability as well as the examples according to the invention, but the MEKO content as an indicator of the butanone oxime content is above the limit requiring labeling.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III a silane of the general formula Rn (RO) m Si (O-Ac) k is not used IV 7.5 parts by weight Vinyl-Si (2-butanone oxime) 1.5 (methoxy) 1.5 be used.
  • a silane of the general formula Rn (RO) m Si (O-Ac) k is not used
  • IV 7.5 parts by weight Vinyl-Si (2-butanone oxime) 1.5 (methoxy) 1.5 be used.
  • the MEKO content in the uncrosslinked product is 0.7% by weight.
  • Example 1 The procedure described in Example 1 is repeated with the modification that III a silane of the general formula Rn (RO) m Si (O-Ac) k is not used IV 4.5 parts by weight Methyltris (2-butanone oxime) silane 3.0 parts by weight vinyltrimethoxysilane be used.
  • Rn (RO) m Si (O-Ac) k 4.5 parts by weight Methyltris (2-butanone oxime) silane 3.0 parts by weight vinyltrimethoxysilane be used.
  • the MEKO content in the uncrosslinked product is 0.7% by weight.
  • the polysiloxane compositions according to Comparative Examples 3 and 4 no longer cured after being stored at 100 ° C for 24 hours and at 50 ° C for one month. They remained pasty after storage.
  • the uncrosslinked product is not stable, but dissolves both shortly after preparation and after storage under the specified conditions.

Claims (12)

  1. Masse de polysiloxane durcissable à la température ambiante, qui contient :
    a) des polysiloxanes réticulables, qui contiennent comme groupes fonctionnels des groupes acyloxyles ;
    b) des réticulants d'alcoxysilane.
  2. Masse de polysiloxane selon la revendication 1, caractérisée en ce que les polysiloxanes contiennent comme groupes fonctionnels des groupes hydroxyles et des groupes acyloxyles.
  3. Masse de polysiloxane selon la revendication 2, caractérisée en ce qu'elle contient comme réticulant un mélange d'alcoxy- et d'oximesilanes et/ou des silanes avec des groupes alcoxyles et oximes dans la même molécule.
  4. Masse de polysiloxane selon la revendication 3, caractérisée en ce que le rapport molaire entre les groupes alcoxyles et les groupes oximes est compris entre 1 : 4 et 4 : 1, de préférence entre 1 : 2 et 2 : 1.
  5. Masse de polysiloxane selon l'une quelconque des revendications 1 à 4, caractérisée en ce que les groupes acyloxyles présentent la formule - O-C=O-R, dans laquelle R est égal à H ou à un radical hydrocarbure à 1 à 8 atomes de C.
  6. Masse de polysiloxane selon la revendication 5, caractérisée en ce que les groupes acyloxyles sont complètement ou partiellement des groupes acétoxyles.
  7. Masse de polysiloxane selon l'une quelconque des revendications 1 à 6, caractérisée en ce qu'elle contient des polydiacyloxysiloxanes.
  8. Masse de polysiloxane selon l'une quelconque des revendications 1 à 7, caractérisée en ce que les réticulants d'alcoxysilane contiennent deux ou plus groupes alcoxyles.
  9. Procédé de production d'une masse de polysiloxane selon la revendication 1, caractérisée en ce qu'on fait réagir des polysiloxanes contenant des groupes hydroxyles réactifs avec des silanes contenant des groupes acyloxyles et en ce qu'on ajoute ensuite ou en même temps des réticulants d'alcoxysilane.
  10. Procédé selon la revendication 9, caractérisé en ce que les polysiloxanes contenant les groupes hydroxyles réactifs sont des polydiorganosiloxanes, de préférence des polydiméthylsiloxanes.
  11. Procédé selon la revendication 9 ou 10, caractérisé en ce que les silanes contenant des groupes acyloxyles sont choisis parmi le groupe qui consiste en :
    a) des silanes de la formule générale :

            Ra(R-O)mSi(O-Ac)k

    dans laquelle Ac représente un radical acyle et R un hydrogène ou un radical hydrocarbure avec 1 à 8 atomes de carbone, substitué le cas échéant, sachant que les R peuvent être identiques ou différents et sachant que l'on a pour les indices :
    k: 1 à4
    m:0 à 2
    n:0 à 2
    k+m+n=4
    b) des mélanges de silanes selon a) avec des silanes qui sont définis comme dans a), mais pour lesquels les indices sont :
    k: 0 à 4
    m:0 à 4
    n:0à4
    k+m+n=4
    c) des produits de condensation partiellement hydrolysés de silanes selon a) ou de mélanges selon b).
  12. Procédé selon l'une quelconque des revendications 9 à 11, caractérisé en ce que la proportion des silanes contenant des groupes acyloxyles, rapportée aux polysiloxanes contenant des groupes hydroxyles réactifs est de 0,01 à 2 % en poids, de préférence de 0,05 à 1,5 % en poids, encore plus préférablement de 0,1 à 0,5 % en poids.
EP02004869A 2002-03-04 2002-03-04 Agent d'étanchéité a base de silicone a durcissement a temperature ambiante Expired - Lifetime EP1342742B1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DE50207717T DE50207717D1 (de) 2002-03-04 2002-03-04 Bei Raumtemperatur aushärtbare Polysiloxan-Masse
AT02004869T ATE335038T1 (de) 2002-03-04 2002-03-04 Bei raumtemperatur aushärtbare polysiloxan-masse
EP02004869A EP1342742B1 (fr) 2002-03-04 2002-03-04 Agent d'étanchéité a base de silicone a durcissement a temperature ambiante
ES02004869T ES2269533T3 (es) 2002-03-04 2002-03-04 Masa de polisiloxano endurecible a temperatura ambiente.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP02004869A EP1342742B1 (fr) 2002-03-04 2002-03-04 Agent d'étanchéité a base de silicone a durcissement a temperature ambiante

Publications (2)

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EP1342742A1 EP1342742A1 (fr) 2003-09-10
EP1342742B1 true EP1342742B1 (fr) 2006-08-02

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EP (1) EP1342742B1 (fr)
AT (1) ATE335038T1 (fr)
DE (1) DE50207717D1 (fr)
ES (1) ES2269533T3 (fr)

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US7591865B2 (en) 2005-01-28 2009-09-22 Saint-Gobain Abrasives, Inc. Method of forming structured abrasive article
US8287611B2 (en) 2005-01-28 2012-10-16 Saint-Gobain Abrasives, Inc. Abrasive articles and methods for making same
US8435098B2 (en) 2006-01-27 2013-05-07 Saint-Gobain Abrasives, Inc. Abrasive article with cured backsize layer
EP1894975A1 (fr) 2006-08-30 2008-03-05 Sika Technology AG Composition de silicone
DE102010001588A1 (de) * 2010-02-04 2011-08-04 Henkel AG & Co. KGaA, 40589 Härtbare Zusammensetzungen mit verbesserten Brandeigenschaften
CN102093720B (zh) * 2010-09-14 2013-01-09 抚顺哥俩好化学有限公司 长贮存期酮肟型室温硫化硅橡胶及其制备方法
JP7327212B2 (ja) * 2019-03-07 2023-08-16 信越化学工業株式会社 二成分型室温縮合硬化性オルガノポリシロキサン組成物

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JPS60210663A (ja) * 1984-04-03 1985-10-23 Seitetsu Kagaku Co Ltd 室温硬化型シリコ−ンエラストマ−組成物
US5508360A (en) * 1995-03-31 1996-04-16 Dow Corning Corporation Moisture-curable hot melt silicone pressure-sensitive adhesives
US5656710A (en) * 1995-06-07 1997-08-12 Loctite Corporation Low viscosity silicone sealant
US6013754A (en) * 1998-01-16 2000-01-11 Courtaulds Coatings, Inc. Heavy Duty Division Catalyst free primer coating compositions

Also Published As

Publication number Publication date
EP1342742A1 (fr) 2003-09-10
DE50207717D1 (de) 2007-08-30
ATE335038T1 (de) 2006-08-15
ES2269533T3 (es) 2007-04-01

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